


Catch 22

by Dmsilvis



Category: Supernatural
Genre: Castiel and Dean Winchester Need to Use Their Words, Castiel and Dean are main pairing, F/F, F/M, Foul Language, Friends With Benefits, Friends to Lovers, Halloween, M/M, Pining, all others are mentions of, all the pining, suggested sexual content
Language: English
Status: Completed
Published: 2018-01-17
Updated: 2018-01-17
Packaged: 2019-03-05 22:49:02
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,664
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13397925
Author URL: https://archiveofourown.org/users/Dmsilvis/pseuds/Dmsilvis
Summary: Their entire town knew that Dean or Cas were a sure thing if you wanted meaningless sex and you were in for a damn good time. Word got around and neither man left their partner wanting when the night was through.DEANA year ago, at this Halloween party, Cas and Dean ended up tumbling into bed together after the festivities. They had been friends for ages and occasionally fuck buddies when one of their dates hadn’t panned out.  Since then, they’ve been a regular for each other but still not exclusive. Dean knew Cas occasionally had other partners and so did Dean.Truth be told, it had been a couple months since Dean got any enjoyment out of sex that wasn’t with Cas.CASTIELCas was leaving his schedule open in case Dean called. It was pathetic but that's what it was. He wanted his best friend around as more than just a hookup, He wanted Dean to himself. He hadn’t enjoyed sex for months unless it was with Dean.  Don’t get him wrong, he still had sex, but there was no connection. He couldn’t leave fast enough when all was said and done.  He always spent the night with Dean though.





	Catch 22

**Author's Note:**

> Thank you TobytheWise for being a beta for this  
> This is just a random idea I needed to get out of my already busy mind.  
> Keep in mind please that I write for pure fun, so any grammar atrocities you may see, or points you don't agree with, be kind and just don't comment on them. This is not something I'm looking for a career in, I wish to simply throw happy thoughts out into the world.  
> Enjoy this pining and fluff :)

Dean loved his hometown. It was just small enough that everyone knew almost everyone but too small to be boring. Regardless, The Roadhouse was still the place to be on weekends. They ran a wing and drink special for happy hour and the crowd never failed to show up. The fact that this was the weekend before Halloween meant that the festivities were even more fun. 

Dean, however, was feeling irritated. He sat, people watching. He took in all the awesome costumes and all the people in various states of dress and undress. Folks really went all out for Ellen’s costume contest. All of the employees voted on best costume. Of course, people put in their best effort when “Free Friday” was what you could win. It pretty much meant that your wings and beer for happy hour were free for a year. 

Benny was currently partaking of his final free Friday beside Dean. He had won last year for a kickass Vampire costume he put together, complete with retractable teeth. His wife, Andrea, came as his bloody victim. They didn’t bother dressing up this year since Ellen had a rule that you couldn’t win two years in a row. Benny was talking about something in between bites of wings and gulps of beer, but Dean wasn’t paying attention. He was busy watching Cas in the corner, who currently had two women hanging off him. April was on one side dressed as an angel, a slutty angel but still an angel. Meg was on the other side, rightfully dressed as a demon. Cas didn’t bother to dress up. He rushed here from work and hadn’t even made it over to talk to Dean yet.

“Brother? You even listenin’ to what I’m sayin’?” Dean turned his head to see Benny and Andrea looking at him expectantly. Dean sighed and shook his head. 

“Sorry Benny, I’m kind of out of it tonight,” Dean got his head into the conversation, “What was that?”

Benny chuckled, “I said, Lisa has been eyeing you all night. I think she found her Halloween candy.” Dean followed Benny’s eye and yes Lisa was smiling at him. He recognized that smile too. He and Lisa had been each other’s one night stands a few times over the years. He winked at her but his heart wasn’t in it. 

His eyes went back to Cas who had lost his demon at some point. He scanned the room and found Meg was currently whispering sweet nothings in Luc’s ear near the karaoke machine. Just as well. Less competition the better. April was still a problem however, still hanging on Cas like he was a crutch as Cas talked to Gabriel and Kali.

Dean’s irritation grew. A year ago, at this halloween party, Cas and Dean ended up tumbling into bed together after the festivities. They had been friends for ages and occasionally fuck buddies when one of their dates hadn’t panned out. Last year was the first time they chose to leave with each other however. Dean remembered how his stomach flip flopped when Dean mentioned Cas should take Meg home and Cas gave him that soul searching stare and said plainly, “I’d rather take you home”. So they ended up at Cas’s apartment. Since then, they’ve been a regular for each other but still not exclusive. Dean knew Cas occasionally had other partners and so did Dean. They were up front about that. The entire town knew that these two guys were a sure thing if you wanted meaningless sex and you were in for a damn good time. Word got around and neither man left their partner wanting when the night was through. Dean downed his drink and asked Ellen for another.

Truth be told, it had been a couple months since Dean got any enjoyment out of sex that wasn’t with Cas. He would leave with people but he could never actually _perform._ But never let it be said that Dean left a partner unsatisfied. He would go down on his partner, rock their world, insist that he was fine and go home. 

Benny told Dean he and Andrea were heading out even though it wasn’t even 8 o’clock yet. Karaoke didn’t begin until 10. Almost as soon as Benny left, the seat was filled again. This time by Lisa. 

“Hey Stranger,” she smiled.

Dean stared at his drink. “Hey Lis, how’s everything?”

“Hmmm. Better if I could convince you to get me out of here before the costume contest. I can’t lose for the 7th year running.” They both laughed. “Or are you waiting for Cas?”

Dean hadn’t realized he was even watching Cas again. April currently had a tongue in his ear and Dean was shaking out of anger more than he cared to admit. He coughed and looked back to Lisa. “Uh…no, I’m not waiting for Cas. I actually don’t feel like company tonight, Lis.” Her face fell and dammit if Dean couldn’t handle that. He knew Lisa was a single mom and nights out were few and far between for her. If she’s here then it’s because she needs to blow off some steam. He cleared his thoughts and gave Lisa his best smile “—but, maybe it’s just the atmosphere. How about we leave and see where the night takes us?” Lisa’s smile was always so bright, and Dean couldn’t not smile back. He paid both their tabs and they left.

***************************

Cas had about had it with April. She was on him from the moment he entered the bar. Sure, he agreed to be part of this ridiculous last minute costume because Meg and April both worked with him. Their idea was to be the devil and angel on someone’s shoulder. Since Cas didn’t feel like dressing up, he agreed to be their straight man when Alfie, the intern, backed out. He said his girlfriend didn’t approve but Cas strongly felt he was intimidated by Meg and April. Meg understood him and while they had shared a bed a few times, she more often than not listened to him pine about Dean. April didn’t care about Dean and was going the extra mile to stake a claim on Cas. It annoyed the shit out of him. He made it perfectly clear that he wasn’t interested tonight. Meg had gone elsewhere until the costume contest was suppose to start. She was eyeing up Luc. Cas had hoped April would wander off as well but he had no such luck. He was making his way toward Dean when he saw Benny leave, but he was stopped by Gabriel and his wife. He was talking with Gabe on autopilot while watching Dean, but when Lisa sat down next to him, he focused his attention on Gabe.

“C’mon cuz, you should really come over to our Halloween party tomorrow.” Gabriel smiled. Cas flinched his head away from April. She had too many drinks in her already and she got incredibly handsy.

“Gabe, I’ll see what I get into tomorrow. Adler is expecting the end of month reports and I may be doing some work from home tomorrow.” Gabe rolled his eyes. He knew Castiel was lying but he didn’t press the matter. In all honesty, he was leaving his schedule open incase Dean called. It was sad, but it was what it was. He and Dean had been each other’s weekly booty call for over a year now but, they hung out a few times a week with no sex involved. Castiel enjoyed it. He wanted to see if Dean wanted more but it was never seemed like a good time to bring it up. When things had changed for Cas, he couldn’t quite peg the date. He hadn’t enjoyed sex for months unless it was with Dean. Don’t get him wrong, he still had sex, but there was no connection. He couldn’t leave fast enough when all was said and done. He always spent the night with Dean though. 

A wet tongue in his ear interrupted his thoughts. He growled under his breath and April mistook that as a growl of pleasure. Gabe chuckled. “K, text me tomorrow Cassie, have fun you two.” He winked and left with Kali to talk to Balthazar. Cas came to his senses just in time to see Dean and Lisa leave out the front door. Fuck.

“April, look, I’m sorry but I need to leave,” Cas spat out.

She laughed, “Yes, we should leave!” She slurred as her eyes were half closed. He put an arm around her waist and walked her over to Meg and Luc.

“Meg, I’m sorry but I can’t stay for the costume contest.” 

Meg smirked, “It’s okay Clarence, I found myself a different angel.” Luc smiled as Meg whispered something clearly filthy in his ear, his headband halo going crooked on his head. Luc wasn’t so much dressed up for the occasion as he was simply there being a smartass and looking for a hookup.

“C’mon little brother, you sure you want to give Meg up for the night?” Luc gave him a devilish look. It should creep Cas out that both he and his brother have slept with the same woman but oddly, he didn’t care. April was currently leaning so heavy on Cas he had thought she passed out. “You’ve got a lightweight there Cas.”

Cas rolled his eyes. “Yes, I’m going to put her in a cab—“

“We’ll take her home,” Meg interrupted. “She lives in my building. Luc and I are leaving anyway, aren’t we stud?”

Luc smiled and ran his hand up Meg’s thigh. “Fuck yes we are!” Then just to make Cas squirm, Luc looked him dead in the eye, “You’re welcome to join us, little brother. Meg was just telling me how she would love to have us both at once.” Cas’ eyes went wide and Meg laughed. 

“Honestly Clarence, when are you going to stop falling into Luc’s traps? Of course I didn’t offer that.” She gave Cas a brief hug and whispered in his ear where noone could her or prove it. “Hang in there, Clarence, Dean will come around.” Cas smiled at her and thanked Luc for making sure April got home okay. The 3 of them left and Castiel planted his butt on a barstool and ordered a double.

*****************************************

Lisa knew Dean’s heart wasn’t in this hook up. His dick wasn’t even in it. She had never known Dean to not rise to the occasion. She would be damned if tonight was a one sided thing. He was kissing his way down her stomach when she stopped him. 

“Dean, hey, stop please.” Dean looked up at her confused.

“Uh---did you say stop?” he chuckled.

“Yes, dumbass.” But she said it with a smile because first and foremost Dean was a friend. Dean sat up and looked her. If she didn’t know any better he looked like he was holding back tears. “Dean, we’ve been friends since high school right?” Dean nodded. “I know how much of a man whore you are, so what’s up?” 

Dean threw his legs over the side of the bed and sat up, setting his elbows on his knees. She glanced at the clock a little after 11pm. She curled up beside him and waited. Dean always took awhile to talk, but she was patient.

3:12 AM and Lisa was getting dressed. Dean eventually started talking about Cas and once the floodgates opened the words didn’t stop for almost 3 hours. He got angry, he cried, he went on and on. He was in love, there was absolutely no doubting that. All of their friends and acquaintances knew it. Hell, some of them had a friendly bet going as to which one of them would crack first and when they would both finally become an exclusive couple. 

Dean had fallen asleep and Lisa lay beside him for a little bit before deciding to get up and go home. Dean wouldn’t have minded if she stayed but she would rather be home. Lisa stepped out on the porch and realised that Dean had driven them here. She had no ride home. She really didn’t like the idea of walking home at that hour. She pulled out her phone to search for a cab service when a voice startled her. 

“Hello Lisa,” She looked up to see Cas on the sidewalk.

“Uh, Hello Castiel. What are you doing walking around at this hour?” Lisa looked back at Dean’s door then up at Cas. 

“I couldn’t sleep. I always go out for fresh air when I can’t sleep.” Cas slowly walked up the sidewalk. “Why isn’t Dean taking you home? That’s not very polite of him,” Castiel looked genuinely angry at this thought.

Lisa chuckled, “Oh,he’s asleep. He doesn’t know I’m leaving. Things didn’t pan out the way I was hoping they would tonight.” She finished ordering her cab via the app and sat on the porch swing to wait. She patted the seat beside her. “Keep me company while I wait for my cab?” 

Castiel walked up and sat beside Lisa. “It looks like I’m everyone’s counselor tonight,” Lisa mumbled. Cas tilted his head and looked at her confused. Lisa almost laughed. “So why can’t you sleep? Didn’t April wear you out enough?”

Cas stared at his hands. “I didn’t take April home. She was too drunk to make a wise decisions.” Lisa laughed. Cas stared at her in confusion. “I don’t understand what’s so funny Lisa?” 

Lisa rolled her eyes. “C’mon between you and Dean, you’ve slept with half this town.”

Cas furrowed his brow but then shrugged and nodded. “I can’t deny that, but I’m not a monster. Sober consent matters….” Lisa chuckled again and Cas felt annoyance. “I still don’t understand what’s so funny.”

“The fact that you and Dean both couldn’t close the deal tonight.” Lisa was staring at Cas with intent now. “It’s not only your rules keeping you from that, it’s because you love each other, isn’t it?” Cas didn’t answer. “Dean spent the night talking to me Cas. Just talking, all about you, how when you leave with someone else, it eats away at him. “

“I only leave with other people because Dean leaves with other people,” Cas said, clearly angry

Lisa looked shocked. “And he only leaves with other people because you have someone besides him hanging all over you.” Lisa reached out and took his hand to get him to look at her. “It’s a catch 22 and if either of you dumbasses actually talked to one another instead of assuming you know what’s up with each other, you could save yourself a lot of pain.”

They sat in silence for a few minutes. Cas sighed. “So I’m guessing everyone knows how we feel?”

Lisa smiled, “Anyone with eyes, Cas.”

Cas was only half joking when he asked, “Yet no one has a problem going home with either of us, even though you know it’s going nowhere.”

Lisa smiled brightly. “C’mon, you boys are legendary in our circle! Who would turn either of you down if given the chance?” She elbowed him in the side and they both chuckled.

Headlights coming down the road caught their attention. The cab pulled up to the curb and honked. Lisa huffed annoyance, “Going to wake up the neighborhood.” Cas walked Lisa to the cab, he nodded at Ash and pulled out his wallet to pay Ash for Lisa’s cab. Lisa stopped him. “Cas you don’t have to pay for my cab” 

Castiel gave a weak smile. “Just consider it payment for your counseling services.” He handed money to Ash and leaned into the window to say bye to Lisa. “Thank you, Lisa.”

Lisa kissed Cas on the cheek. “I didn’t lock Dean’s door behind me. You might want to check on him.” She winked as he stepped away from the car. He turned and walked back to Dean’s porch.

He sat down on the porch swing, not quite ready to face the conversation. Lisa said Dean loved him. He needed to hear it from Dean, but getting Dean to talk about his emotions was like making a dog meow. It just wasn’t his native tongue.

“Cas?” Castiel jumped. He saw Dean staring sleepily out of his screen door. 

“Hello Dean.” They stared at each other and after a few seconds Dean seemed to come to his senses. 

Dean opened the screen door and sat on the swing beside Cas. “Not that I ain’t happy to see you man, but have you seen Lisa? She was—“

“She caught a cab home,” Cas interrupted. “I sat and talked to her until she was safely in the cab.”

Dean looked terrified “Ta—talk—talked, about what?”

Cas tried to hide his smile “I couldn’t sleep and—“

“—yeah you were out walkin’, I know how you are,” Dean said.

Silence

Dean cleared his throat. “April was mighty friendly tonight, you end up going home with—“

“NO!” Cas didn’t mean to scream it but he practically did. He looked almost shy and more calmly said “No, no she---I didn’t want to go home with her.”

“Yeah, I know that feeling.” Dean wouldn’t look at him “I didn’t want to go home with Lisa either.”

“Then why did you?” Cas asked with more angry than he meant to but he needed to hear from Dean, everything that Lisa said, but he didn’t want to betray Lisa’s trust.

Dean looked at him, best he could in the low porch light, “Because April had her tongue in your ear and I thought you were taken for the night.”

Cas was now angry and his words came out through gritted teeth. “If you paid attention Dean, she was all over me! I wasn’t returning the advances!” Cas stood up, “What are we Dean?”

Dean sat there dumbfounded. Cas was angry. Cas rarely got angry and it had never, to this day been directed at Dean. Maybe he needed to let all his emotions out in order to get Dean to face his own.

Cas ran his hands through his hair and Dean smirked. Cas knew he just gave himself “sex hair” as Dean referred to it and he knew how much Dean liked that look. “Don’t smirk at me you asshole. I asked you a serious question!”

Dean bit his lip before settling his eyes on Cas’ shoes. “We’re friends with benefits, Cas”

Cas rolled his eyes. “Okay, let me rephrase. What do you WANT us to be Dean?” Cas felt like the next 10 seconds were an hour before Dean cleared his throat and whispered something Cas didn’t hear. “What was that?”

Dean took a deep breath. “Exclusive! I said I want us to be exclusive.” His entire body sagged and he laid his head back on the porch swing and shut his eyes. “I didn’t sleep with Lisa. Fuck, I haven’t gotten off with anyone but you in months! I can’t even get it up for anyone else. I want to go to sleep with you. I want dinner, and – dates—and movies. I want everyone to know you are mine—“

Cas sighed, “Dean,” but Dean kept talking with eyes shut, moving the porch swing slightly while he vomited his feelings without realising it.

“I want to hear about your sucky day and that asshole ,Adler, and I want boring days where we have nothing to do. I want morning coffee and late night walks when you can’t sleep or better yet, late night sex when you can’t sleep---“

“Dean,” Cas tried again but Dean wasn’t listening. Cas just smiled and watched him continue his rant.

“I want to come home to you Cas, shit your lease is up at the end of the year –“

Cas’ eyes went wide, “Dean?”

“-And I practically own this place. Another few years and it’s paid off. Half your shit is here already!”

Cas stopped and simply stared at Dean who still had his eyes shut. Did Dean just ask him to move in?

“Do you know how it feels when I pull one of your shirts out of my laundry, or see that stupid ass health drink in my fridge that I most certainly don’t drink. I keep honey and tea here, i dont drink that either! Your toothbrush is in my bathroom for god sake!” Dean was almost yelling now. “Cas, I can’t keep watching you take home random hook ups! It fucking kills me! And you know wha-----“

Cas stepped forward and raised his voice, “DEAN!”

Dean was shocked into silence when Cas suddenly stopped the movement of the porch swing. He opened his eyes to find his head bracketed by Cas’s arms on either side, staring into eye’s that he knew were so very blue, while Cas leaned down into Dean’s space.

He kissed Dean, slowly, softly. He pulled away but straddled Dean’s lap and while Dean slowly moved the swing again with his foot. “Dean, did you just ask me to be your boyfriend and move in with you all in one go?”

“Yeah I think I did,” Dean was now grinning like an idiot. “Whatdya say Cas?”

Cas kissed him again for who knows how long. They kissed as Cas ground his hips against Dean, who was now more than hard, and it was getting uncomfortable. Then Cas chuckled. “It seems like performance isn’t an issue anymore.”

Dean was kissing his neck, “Never with you.” He spoke deep into Cas’s ear, “I need an answer Cas, are we—“

“Yes Dean, we’re officially a “we” now. How about we move this inside? I want my boyfriend to fuck me senseless.”

“Yes Sir,” Dean growled and Cas let out an embarrassing yelp when Dean got up and picked Cas up with him. They fumbled into the house, locking the door behind them. No one saw or heard from them until Monday morning.


End file.
